


The Halloween I Lost My Virginity

by littlefirefly31



Series: Kink/Request Fics [2]
Category: Supernatural RPF
Genre: Crossdressing, M/M, Popular!Jensen, Rimming, Shy!Jared, cheerleader!Jensen, virgin!Jared
Language: English
Status: Completed
Published: 2014-05-13
Updated: 2014-05-13
Packaged: 2018-01-24 13:49:38
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,900
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1607405
Author URL: https://archiveofourown.org/users/littlefirefly31/pseuds/littlefirefly31
Summary: <blockquote class="userstuff">
              <p>Jared's always had a bit of a crush on Jensen Ackles. When he shows up to a Halloween party dressed as a cheerleader, makeup included, how was Jared supposed to resist?</p>
            </blockquote>





	The Halloween I Lost My Virginity

**Author's Note:**

> Again, if you want a kink written, comment here! I'll write pretty much anything, wincest or J2. I'm gonna start a series of just short-ish kink fics. and i changed the crossdressing prompt up a little bit, instead of jock!jared i had a shy!jared, but i hope its still likeable!!

[Livejournal: ](http://littlefirefly31.livejournal.com/1541.html)

 

Jared had been watching Jensen Ackles for years. No, that sounds too stalker-ish. Jared had been lusting after Jensen Ackles for years. It was a little more normal because it was only rational to lust after Jensen Ackles. He was beautiful. Exceedingly so, with his full, pink lips and green eyes with eyelashes long enough to be a girl’s. It was hard to call him handsome with his features. No, Jensen wasn’t handsome. He was beautiful.

Jensen was a cheerleader and constantly had a swarm of girls around him. He was beautiful and clever. Girls and even a few boys were either envious of him, in love with him, or both. But Jensen wouldn’t even know the name of a shy bookworm that spent lunch in the corner, staring at Jensen and willing him to look over.

It didn’t matter how many times Chad told him he was a pathetic mess and he should get over Jensen. But Jensen’s full, pouty lips and long eyelashes were too addicting for Jared to just “get over.”

Jared was absentmindedly chewing on his sandwich when Chad dropped his lunch tray loudly. “C’mon,” Chad urged. “Sophia said that Danneel was having a party. Danneel invited Sophia, Soph invited me, and I’m inviting you.”  
“I really don’t want to go to Danneel Harris’s Halloween party,” Jared whined. “It’s gonna be cheerleaders and football jocks.”

“I thought Jensen Ackles was a cheerleader,” Chad said. “Wouldn’t you want to see him?”  
Jared sighed. “But you’ll go off with Soph, and then I’ll be alone with a bunch of people I don’t want to be with.”  
“Find some ass to fuck,” Chad suggested. “Might get your mind off Jensen Ackles.”

“I don’t _want_ some random ass to fuck,” Jared whined. “I want _Jensen’s_ ass.”  

“Well you’re not going to get Jensen’s ass, so you might as well get it from someone else,” Chad replied. “I’m sure there are plenty of boys out there who will willingly bend over for you.”  
Jared frowned. “Don’t be so crude.”  
“Whatever, Jay, I tell it like it is. So come on, let’s go to the party.” Chad tapped his watch. “It’s tonight.”

“I’m not going.”  
Chad snorted. “Whatever you say.” He smirked. “But just so you know, I heard along the grapevine-,”  
“Sophia,” Jared interrupted.

“-that Jensen’s costume is going to be—and I can’t believe I’m saying this—incredibly sexy. So. It’s a pity that you’re not going.”

*  
Which is how, 8 hours later, Jared found himself in a horrid vampire costume, fake-fangs and all. “This is humiliating.”

Chad, in his slightly better zombie costume, shrugged. “Well, maybe Jensen will think your pale, vampire-y self is just too hot not to kiss. And fuck.”

Jared groaned. “I really hope so. Because I’m not ever going to put this ridiculous fucking outfit on again.”

Chad insisted on driving his truck, because according to Chad, girls loved sex in trucks. Jared rather doubted it.

Danneel’s house was practically vibrating with the music. People had spilled out onto the lawn and empty cups littered all around them. Jared looked around the house with wide eyes. He’d never been inside a house as big as this one. The music hurt his ears and bodies grinded against each other on a makeshift dance floor in the middle of the room.

“Hey, you came,” Sophia sidled up to them and kissed Chad’s cheek. “Nice to see you too, Jared. How are you?”  
“I’m good,” Jared mumbled. He hoped Sophia didn’t notice his scanning the room for Jensen, but he was never that lucky.

“Who’re you looking for?” She asked.

Jared mumbled, “No one,” at the same time Chad said, “Jensen Ackles.”

“Oh, you’re looking for Jenny?” Sophia smirked. “I think he’s with Danneel.”  
Chad snickered. “Jenny?”  
“He’d never let us call him that usually, but tonight—tonight it seems appropriate,” Sophia replied.

Jared’s eyebrows crinkled. “What?”

“Take a look,” Sophia said. “He’s over there, standing next to Danni.”

Jared raised his eyes to the corner and felt his mouth drop open. Jensen’s costume _was_ sexy. It was unreal, and gorgeous, and revealing, and completely, utterly _feminine_.  
“I know, he looks gorgeous,” Sophia said. “That’s my cheerleading outfit, by the way. It was a little too small on him but it was what Danneel wanted.”  
“What Danneel wanted?” Jared repeated. “What does that mean?”

“Jensen lost a bet, the idiot. The stakes were that whomever one could pick the Halloween costume for the other one. That’s why Danneel wanted so many people here tonight, so everyone could see Jensen in his tight little cheerleader outfit. It’s such a shame he’s gay.”  
Jared perked up. “He’s gay?”  
“You interested?” Sophia’s eyes gleamed. “I could probably introduce you.”

“No!” Jared exclaimed. “I mean, no thank you.”

“So, you’ve been lusting after this guy for weeks—don’t deny it, Jared—and Sophia offers to introduce you and you say _no_? Is there a brain inside that vampire head of yours?” Chad asked incredulously.

Jared blushed. “Not dressed like _this_.”  
“You do look ridiculous,” Chad agreed. “And you’d probably make a bumbling idiot out of yourself.”  
Sophia swatted Chad’s stomach. “He would not!”  
“I would,” Jared admitted. “He makes me stupid.”

“Jensen does have that effect,” Sophia agreed. “I’ve become immune but at first I was tripping over my own feet to be next to him.”

“I’m gonna go get a drink,” Jared decided. “I’ll be right back.”

“Coward,” Chad yelled after him. Jared ignored him and found his way into the kitchen.

Jared didn’t really want a beer. He didn’t think the bitter taste was appealing and being drunk wasn’t worth the hangover the next morning. But it seemed like the only things offered had some alcohol content. Jared picked up a cup and sniffed at it. Vodka and something sweet.  

“Alcohol’s not your thing?” A deep voice said behind him.  

Jared jumped and sloshed the drink on his shirt—not that it mattered since the costume was hideous—but Jensen looked amusedly at him. Jared was as red as a firetruck. “N-n-not really,” Jared stammered.

“Then this doesn’t seem like the party for you.” Jensen stepped closer and he saw pink gloss on his lips and his eyes lined in kohl. His eyelashes didn’t have any makeup on them and Jared supposed that they were feminine enough without makeup.

“I—uh—my friend-,” Jared blushed. He couldn’t even get a word out.

“Your friend dragged you along?” Jensen grabbed a beer and twisted the top off. “Who?”  
“Chad. Chad Michael-,”  
“-Murray,” Jensen finished. “I’ve heard about him from Sophia. Is he really as dickish as he sounds?”

“Unfortunately,” Jared grumbled. “But he’s still my friend.” He tried to lean on the island in the kitchen and ended up slipping and falling forward. It was only Jensen’s arms that kept him upright. Jared groaned. This was by far the most embarrassing moment of his life.  

“It can’t be the most embarrassing moment of your life,” Jensen replied.

“Oh, fuck I said that aloud,” Jared whined. “Just kill me now.”

Jensen chuckled. “You’re too cute to kill.”

Jared was suddenly hyper-aware of everywhere his body was in contact with Jensen’s. “I—cute—what?”

Jensen straightened Jared up and pressed him against the fridge. “You think I haven’t noticed you watching me? I see you sitting at the table in the cafeteria and thinking you’re being sneaky, sitting in the library and trying to disguise you watching me as reading your books—I’ve noticed you, Jared Padalecki.”

 _Oh god, he knows I’m stalking him_. “You know my name?” Jared realized. “How do you know my name?”

Jensen slid his hands into Jared’s back pockets and he smelled so sweet and he was smirking and he was the hottest “girl” that Jared had ever seen in his entire life. To his dismay, his dick started to get interested as well. Jensen’s body was up against his and Jensen would definitely be able to tell that Jared was getting hard for him.

“I noticed you watching me. I thought your blush was damn cute and I asked around. Turns out you’re smart, huh?” Jensen ran a finger down Jared’s neck and his whole body shuddered. “Shy, too. I love that I can make you blush.” His voice dropped. “Are you shy in bed, too? Do you blush when you have your clothes peeled off, when you see a big, fat cock-,” Jensen smirked. “Or are you a virgin?” Jared shifted, embarrassed. Jensen’s face lit up. “Oh you _are_! Oh baby.”  
“I know, it’s humiliating,” Jared mumbled.

“Humiliating?” Jensen kissed Jared’s neck lightly. “Oh no. Baby, that’s so sexy. It’s making me so hot, thinking about you completely untouched. Have you fantasized about it? About being fucked? Or are you a top? Pounding into my ass, hearing me pant your name?”

Jared’s breath stuttered because that was basically his entire sexual fantasy ever. Except now it featured Jensen in Sophia’s skimpy cheerleading outfit. “Jensen…”  
“I’m right, aren’t I?” Jensen purred. He licked Jared’s neck and Jared keened. “Wanna fuck me in the kitchen? Anyone could walk in and see me begging, see you fucking me into the table… God, I saw your fangs and could only think about you biting me, sucking on me.”

Jared whimpered. He was so hard it hurt. “Take me upstairs,” Jensen whispered. “Put your hand up my skirt. Sound good?”  
“Yes,” Jared breathed. “Very good.”

“C’mon, gorgeous, let’s go.” Jensen nipped at his ear and Jared’s knees turned to jelly.

“I don’t know if I can walk,” Jared murmured.

“Shame.” Jensen leaned up and put his lips against Jared. “I was really looking forward to having sex with you.”

Jared found a sudden burst of strength and hooked his arms under Jensen’s legs. Jensen wrapped his limbs around Jared and he attacked his lips again. “Jen—I can’t walk if you’re—fuck—kissing me like that.’

“But you taste really sweet.” Jensen nipped his lip and it was almost impossible to find his way up the stairs without throwing Jensen down and fucking him.

“I hate you,” Jared groaned. He managed to worm his way into what must have been the guess bedroom before dumping Jensen on his bed.

“Take my clothes off,” Jensen demanded. “Wait. Take yours off first. I wanna see if the rest of you is as hot as your blush.”

Jared peeled his shirt off and tried to hide his scrawny frame. “No hiding,” Jensen demanded. “I want to see every inch of you.” He reached forward and rolled Jared’s nipple around in his fingers. Jared moaned and arched into the touch. “Didn’t know this felt good, did you? What _have_ you done, my cute little virgin?”

“N-n-not much,” Jared stuttered. “Jerked off. Nothing else, really.”

“Hm…” Jensen tapped his chin like he was thinking. “Never had anything up your ass?” Jared shook his head. “It feels so good, Jared, you have no idea. It’s weird the first time but then it’s nice. We might trade off, how’s that? I’m usually a bottom but I think I could probably switch to get a chance at your gorgeous ass.” He nipped Jared’s lip. “Of course, if you’re proportional, it might be hard for me _not_ to beg for your cock up my ass.”

Jared shuddered and struggled to get his belt undone and shove down his jeans. When he was only in his boxers, he rolled Jensen onto his back and pushed his arms above his head. Jared slid his hands under the cheerleading skirt and stroked across his soft thighs. His fingers ran into lacy material and Jared’s dick twitched. “Take this off,” He demanded. To his pleasure, Jensen acquiesced until the fabric was on the ground.

Jared moaned when his body was revealed. A red, lacy garter belt decorated his thighs and cock. The panties were small and the line of his thick cock was easily visible. It was huge and tempting, almost as big as Jared. He stroked a finger down the sensitive organ and Jensen keened. “More,” he panted.

Jared leaned down and mouthed at Jensen’s cock through the lace. His fingers stroked across the lace on his thighs and reveled at how pretty Jensen was. He was smoking hot and more gorgeous than any girl. And Jensen was moaning and begging because of _Jared_.

It was quite possibly the best moment of his entire life.

A wet spot spread on Jensen’s panties from Jared’s saliva and Jensen’s dripping cock. “God, you’re leaking for me,” Jared breathed. “Are you hard, Jen? How does it feel when I stroke you through your underwear? I bet it feels wonderful. My hand massaging your balls, lace rubbing against your cock… I wish you could see how hot you are. It’s driving me _mad_.”  
“Take your boxers off,” Jensen whined. “I wanna see you, wanna taste you.” Jared complied and Jensen’s pupils blew wide with lust. “Lemme suck you, Jay, can I suck you?”

Jensen wanted those perfect, full, girly lips around his cock. “Yes.” He shuffled forward until he was straddling his chest and his cock was brushing against Jensen’s lips. Jensen opened his mouth and Jared’s cock was surrounding by the most delicious wet mouth that his cock had ever been in. Well, it was his first blowjob, but still it was fantastic.

Jensen pulled off momentarily. “Fuck my mouth, Jay!”

Jared pulled out and pushed back in gently. He didn’t want to choke Jensen, but he glared at him as if to say _I’m not going to break, asshole_. Jared pushed in harder and Jensen kept steadily sucking and Jared thought he might die from the pleasure before he actually came. Jensen’s tongue started to trace the vein under Jared’s dick and he whimpered. “I’m gonna come, Jen-,” He tried to pull out but Jensen flung his hands up and squeezed Jared’s hips. He couldn’t hold on any longer and came down Jensen’s through. He swallowed it all and Jared pulled his soft dick out.

Jensen was so hard the tip of his dick was peeking out from under his panties. “You taste amazing,” Jensen moaned. “I want to feel that dick up my ass, Jared, _now_.” Jared really didn’t want to take the garter belt off. It was too fucking hot. “Then peel it down and fuck me with it around my thighs,” Jensen growled. Jared hadn’t meant to say that last part aloud.

“Roll onto your stomach,” Jared said. “’M gonna prep you.”

“You better, before you shove your monster cock up my ass,” Jensen grumbled. He sounded more lustful that cranky, though.

Jared pulled the panties down just enough to expose Jensen’s ass. It was smooth and hard and Jared couldn’t help but stroke and squeeze the perfect ass. Jared leaned down and parted Jensen’s cheeks. Tentatively he ran his tongue across Jensen’s hole. He’d seen people in porn do it and watched their partner moan and squirm in pleasure. Jensen had the same reaction, pushing his ass into Jared’s mouth.

Jensen tasted weird at first, but he quickly got used to it and even wiggled his tongue inside. Jensen was a whimpering mess and Jared started to push his fingers through the spit-slick hole. But Jared was big, and he didn’t want to push in on saliva alone. “Lube?”  
“Nightstand,” Jensen panted. Jared reached over to grab it and quickly opened it to smear it onto his fingers. Jensen was already partially stretched from Jared’s tongue and fingers, but he still scissored Jensen open until he was threatening Jared with pain unless he fucked him.

Jared slowly pushed in, the lacey belt brushing against Jared’s thighs. If Jared thought Jensen’s mouth was good, it was nothing compared to the feeling of his tight ass.

“Move,” Jensen snapped when Jared was fully inside. Jared eagerly pulled out and shoved back in, pushing Jensen forward slightly with the force of his thrusts. He knew if he hit Jensen’s prostate it would feel like stars, and so he adjusted his hips several times until Jensen screamed and bucked. “More! More!”

Jared willingly complied, fucking Jensen hard and rolling his hips slowly. Jensen was rubbing his dick against the sheets and Jared growled. “No,” He demanded. “Stay still.”

He pushed his hand under Jensen and started to rub lightly across Jensen’s dick. It wasn’t enough to make Jensen come and Jensen babbled out threats through moans and pleas. Jared took pity on the pretty boy and jacked him harder, slamming against Jensen’s prostate on each thrust.

Jensen tightened up and then with a strangled cry he was coming on the bedspread. Jared howled and came right after him. When it was too much, he pulled out and flopped next to Jensen.

“That was awesome,” Jared muttered.

Jensen chuckled. “Losing your virginity was worth it?”  
“Best _ever_ ,” Jared said.

“Not that you have much to compare it to,” Jensen pointed out.

“I fucked a crazy hot guy with a garter belt shoved down around his thighs and came twice. I don’t think anything will ever come close to this,” Jared replied.

“Hm, glad I made it good for you.” Jensen rolled over and tucked his head into Jared’s neck. “Orgasms make me sleepy.”

“My parents…”  
“Text them and staying with a friend,” Jensen demanded. “You owe me another orgasm.”

Jared chuckled. “You got it, Jen.”  

 

 


End file.
